IL41809A - Trifluoromethyl-salicylanilides and process for preparing them - Google Patents
Trifluoromethyl-salicylanilides and process for preparing themInfo
- Publication number
- IL41809A IL41809A IL41809A IL4180973A IL41809A IL 41809 A IL41809 A IL 41809A IL 41809 A IL41809 A IL 41809A IL 4180973 A IL4180973 A IL 4180973A IL 41809 A IL41809 A IL 41809A
- Authority
- IL
- Israel
- Prior art keywords
- trifluoromethyl
- grams
- formula
- salicylanilide
- nitro
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- XWLKIJOJBDAUOO-UHFFFAOYSA-N n-phenyl-2-(trifluoromethoxy)benzamide Chemical class FC(F)(F)OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 XWLKIJOJBDAUOO-UHFFFAOYSA-N 0.000 title description 5
- 229950000975 salicylanilide Drugs 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000460 chlorine Substances 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 230000000802 nitrating effect Effects 0.000 claims abstract description 3
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 13
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- -1 phenyl ester Chemical class 0.000 claims description 12
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 11
- 229960004889 salicylic acid Drugs 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012320 chlorinating reagent Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 5
- 230000000507 anthelmentic effect Effects 0.000 abstract description 4
- DVIHKVWYFXLBEM-UHFFFAOYSA-N 2-hydroxybenzoyl chloride Chemical class OC1=CC=CC=C1C(Cl)=O DVIHKVWYFXLBEM-UHFFFAOYSA-N 0.000 abstract description 3
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical class OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 3
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 77
- 239000000243 solution Substances 0.000 description 23
- 238000004458 analytical method Methods 0.000 description 19
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000003931 anilides Chemical class 0.000 description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 8
- 229910017604 nitric acid Inorganic materials 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 150000001448 anilines Chemical class 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 241000242711 Fasciola hepatica Species 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical compound CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- AQGIHCYSEBURIJ-UHFFFAOYSA-N 2-hydroxy-3-nitro-4-(trifluoromethyl)benzoic acid Chemical compound FC(C=1C(=C(C(C(=O)O)=CC1)O)[N+](=O)[O-])(F)F AQGIHCYSEBURIJ-UHFFFAOYSA-N 0.000 description 4
- QEJQOCDJAIKMOH-UHFFFAOYSA-N 2-hydroxy-5-nitro-4-(trifluoromethyl)benzoyl chloride Chemical compound FC(C=1C=C(C(C(=O)Cl)=CC=1[N+](=O)[O-])O)(F)F QEJQOCDJAIKMOH-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 244000045947 parasite Species 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- XMLFPUBZFSJWCN-UHFFFAOYSA-N 2-Hydroxy-4-trifluoromethyl benzoic acid Chemical compound OC(=O)C1=CC=C(C(F)(F)F)C=C1O XMLFPUBZFSJWCN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000000973 chemotherapeutic effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 208000006275 fascioliasis Diseases 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 210000000232 gallbladder Anatomy 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- XULACPAEUUWKFX-UHFFFAOYSA-N niclofolan Chemical compound C1=C(Cl)C=C([N+]([O-])=O)C(O)=C1C1=CC(Cl)=CC([N+]([O-])=O)=C1O XULACPAEUUWKFX-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- XLYCPDAZPXWJLN-UHFFFAOYSA-N 2-hydroxy-3-nitro-4-(trifluoromethyl)benzoyl chloride Chemical compound FC(C=1C(=C(C(C(=O)Cl)=CC1)O)[N+](=O)[O-])(F)F XLYCPDAZPXWJLN-UHFFFAOYSA-N 0.000 description 2
- GLOYNFBUFTXVOI-UHFFFAOYSA-N 2-hydroxy-5-nitro-4-(trifluoromethyl)benzoic acid Chemical compound FC(C=1C=C(C(C(=O)O)=CC1[N+](=O)[O-])O)(F)F GLOYNFBUFTXVOI-UHFFFAOYSA-N 0.000 description 2
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 description 2
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 2
- CDIDGWDGQGVCIB-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CDIDGWDGQGVCIB-UHFFFAOYSA-N 0.000 description 2
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000283903 Ovis aries Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- ICKMASVVMCGZLR-UHFFFAOYSA-N [2-[(4-chlorophenyl)carbamoyl]-4,6-diiodophenyl] acetate Chemical compound CC(=O)OC1=C(I)C=C(I)C=C1C(=O)NC1=CC=C(Cl)C=C1 ICKMASVVMCGZLR-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 159000000009 barium salts Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 229950010946 clioxanide Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 229950006977 niclofolan Drugs 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- KPOAJXVOFXDTJM-UHFFFAOYSA-N 2-hydroxy-3,5-dinitro-4-(trifluoromethyl)benzoic acid Chemical compound FC(C=1C(=C(C(C(=O)O)=CC1[N+](=O)[O-])O)[N+](=O)[O-])(F)F KPOAJXVOFXDTJM-UHFFFAOYSA-N 0.000 description 1
- AWBMMILWHXHEQM-UHFFFAOYSA-N 2-nitrooxy-4-(trifluoromethyl)benzoic acid Chemical compound FC(C=1C=C(C(C(=O)O)=CC1)O[N+](=O)[O-])(F)F AWBMMILWHXHEQM-UHFFFAOYSA-N 0.000 description 1
- RQBHTTDLFFGKJR-UHFFFAOYSA-N 3,5-dimethylaniline;hydrochloride Chemical compound Cl.CC1=CC(C)=CC(N)=C1 RQBHTTDLFFGKJR-UHFFFAOYSA-N 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- QOWUTCSJIRILJB-UHFFFAOYSA-N FC(C=1C(=C(C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F)=CC1[N+](=O)[O-])O)[N+](=O)[O-])(F)F Chemical compound FC(C=1C(=C(C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F)=CC1[N+](=O)[O-])O)[N+](=O)[O-])(F)F QOWUTCSJIRILJB-UHFFFAOYSA-N 0.000 description 1
- DGDGJEJBHUZHON-UHFFFAOYSA-N FC(C=1C(=C(C(C(=O)NC2=CC=C(C=C2)Cl)=CC1)O)[N+](=O)[O-])(F)F Chemical compound FC(C=1C(=C(C(C(=O)NC2=CC=C(C=C2)Cl)=CC1)O)[N+](=O)[O-])(F)F DGDGJEJBHUZHON-UHFFFAOYSA-N 0.000 description 1
- 208000006968 Helminthiasis Diseases 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 241000242541 Trematoda Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- KBLWCSLCJQJMDZ-UHFFFAOYSA-N [N+](=O)([O-])C=1C(=C(C(C(=O)NC2=CC=CC=C2)=CC1)O)[N+](=O)[O-] Chemical compound [N+](=O)([O-])C=1C(=C(C(C(=O)NC2=CC=CC=C2)=CC1)O)[N+](=O)[O-] KBLWCSLCJQJMDZ-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 244000144980 herd Species 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C205/60—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms in ortho-position to the carboxyl group, e.g. nitro-salicylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722213607 DE2213607C3 (de) | 1972-03-21 | Trifluormethyl-salicylanilide, Verfahren zu ihrer Herstellung und pharmazeutische Präparate, die diese Verbindungen enthalten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL41809A0 IL41809A0 (en) | 1973-05-31 |
| IL41809A true IL41809A (en) | 1977-04-29 |
Family
ID=5839590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41809A IL41809A (en) | 1972-03-21 | 1973-03-19 | Trifluoromethyl-salicylanilides and process for preparing them |
Country Status (13)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5513084Y2 (enrdf_load_stackoverflow) * | 1975-07-08 | 1980-03-24 | ||
| JPS55129256A (en) * | 1979-02-28 | 1980-10-06 | Isao Ozawa | Antifungal compound |
| JPS58104799A (ja) * | 1981-12-18 | 1983-06-22 | 株式会社パイロット | ボ−ルペンチツプの製造方法 |
| JPH0768185B2 (ja) * | 1986-12-23 | 1995-07-26 | セントラル硝子株式会社 | ニトロ置換４―トリフルオロメチル安息香酸の製造方法 |
| JPH0768183B2 (ja) * | 1986-12-23 | 1995-07-26 | セントラル硝子株式会社 | ５―トリクロロメチル―２―トリフルオロメチルニトロベンゼンおよびその製造法 |
| DE4110483A1 (de) * | 1991-03-30 | 1992-10-01 | Bayer Ag | Substituierte salicylamide, mittel gegen pflanzenkrankheiten |
| CN100370975C (zh) * | 2000-12-18 | 2008-02-27 | 株式会社医药分子设计研究所 | 炎症性细胞因子产生游离抑制剂 |
| CN100464742C (zh) * | 2002-06-10 | 2009-03-04 | 株式会社医药分子设计研究所 | NF-κB活化抑制剂 |
| WO2003103655A1 (ja) * | 2002-06-10 | 2003-12-18 | 株式会社医薬分子設計研究所 | 癌治療剤 |
| CN111302968B (zh) * | 2020-03-20 | 2021-06-08 | 中国科学院上海有机化学研究所 | 一种酰胺氮三氟甲基化合物的合成方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE615511A (enrdf_load_stackoverflow) * | 1961-03-25 | |||
| FR1318207A (fr) * | 1961-03-25 | 1963-02-15 | Cassella Farbwerke Mainkur Ag | Arylamides d'acides salicyliques et leur procédé de préparation |
| GB1048084A (en) * | 1963-08-14 | 1966-11-09 | Ici Ltd | Benzanilide derivatives |
| CH477163A (de) * | 1967-07-26 | 1969-10-15 | Ciba Geigy | Verwendung von Salicylsäure-o-hydroxyphenylamiden zum antimikrobiellen Ausrüsten bzw. zum Schützen von textilem Material gegen schädliche Mikroorganismen |
| DE1668080A1 (de) * | 1968-01-18 | 1971-07-22 | Hoechst Ag | Verfahren zur Herstellung von 3-Nitro-gamma-resorcylsaeureaniliden |
-
1973
- 1973-03-15 US US341559A patent/US3906034A/en not_active Expired - Lifetime
- 1973-03-15 EG EG100/73A patent/EG10942A/xx active
- 1973-03-16 NL NL7303717A patent/NL7303717A/xx unknown
- 1973-03-16 CA CA167,231A patent/CA1007653A/en not_active Expired
- 1973-03-16 JP JP48030750A patent/JPS495941A/ja active Pending
- 1973-03-19 CH CH1266676A patent/CH587230A5/xx not_active IP Right Cessation
- 1973-03-19 GB GB1306373A patent/GB1413226A/en not_active Expired
- 1973-03-19 CH CH398673A patent/CH583182A5/xx not_active IP Right Cessation
- 1973-03-19 IL IL41809A patent/IL41809A/en unknown
- 1973-03-19 CH CH1266776A patent/CH587231A5/xx not_active IP Right Cessation
- 1973-03-20 ZA ZA731945A patent/ZA731945B/xx unknown
- 1973-03-20 AT AT246173A patent/AT324312B/de not_active IP Right Cessation
- 1973-03-20 HU HUHO1553A patent/HU166711B/hu unknown
- 1973-03-20 FR FR7309898A patent/FR2182881B1/fr not_active Expired
- 1973-03-21 BE BE129076A patent/BE797116A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2182881A1 (enrdf_load_stackoverflow) | 1973-12-14 |
| CH587231A5 (enrdf_load_stackoverflow) | 1977-04-29 |
| US3906034A (en) | 1975-09-16 |
| JPS495941A (enrdf_load_stackoverflow) | 1974-01-19 |
| CA1007653A (en) | 1977-03-29 |
| NL7303717A (enrdf_load_stackoverflow) | 1973-09-25 |
| IL41809A0 (en) | 1973-05-31 |
| HU166711B (enrdf_load_stackoverflow) | 1975-05-28 |
| DE2213607A1 (de) | 1973-09-27 |
| BE797116A (fr) | 1973-09-21 |
| DE2213607B2 (de) | 1976-07-29 |
| EG10942A (en) | 1976-11-30 |
| FR2182881B1 (enrdf_load_stackoverflow) | 1976-10-22 |
| AU5341573A (en) | 1974-09-19 |
| CH583182A5 (enrdf_load_stackoverflow) | 1976-12-31 |
| ZA731945B (en) | 1974-01-30 |
| CH587230A5 (enrdf_load_stackoverflow) | 1977-04-29 |
| AT324312B (de) | 1975-08-25 |
| GB1413226A (en) | 1975-11-12 |
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